Article
  • Thermotropic Liquid Crystalline Properties of Cholesteryloxycarbonated and (8-Cholesteryloxycarbonyl) heptanoated Disaccharides
  • Jeong SY, Ma YD
  • 콜레스테릴옥시카본화 그리고 (8-콜레스테릴옥시카보닐)헵타노화 이당류들의 열방성 액정 특성
  • 정승용, 마영대
Abstract
Fully cholesteryloxycarbonated and (8-cholesteryloxycarbonyl)heptanoated disaccharide derivatives were synthesized by reacting cellobiose, maltose, and lactose with cholesteryl chloroformate or 8-cholesteryloxycarbonylheptanoyl chloride, and their thermotropic liquid crystalline properties were investigated. All the cholesteryloxycarbonated derivatives(CH1DSs) formed enantiotropic cholesteric phases, whereas all the (8-cholesteryloxycarbonyl)heptanoated derivatives(CH8DSs) exhibited monotropic cholesteric phases with left-handed helicoidal structures whose optical pitches(λm's) decrease with increasing temperature. All the CH1DSs, contrast with the CH8DSs, did not display reflection colors over the full cholesteric range, suggesting that the helicoidal twisting power of the cholesteryl group highly depends on the length of the spacer joining the cholesteryl group to the disaccharide chain. The thermal stability and degree of order in the mesophase and the temperature dependence of the λm observed for CH8DSs were entirely different from those reported for the cholesterol-bearing dimers and triplet and the (8-cholesteryloxycarbonyl)heptanoated polysaccharide derivatives. The results were discussed in terms of the difference in the number of the mesogenic units per mole of repeating unit and the flexibility of the main chain.

셀로비오스, 말토오스 그리고 락토오스를 콜레스테릴 클로로포메이트 또는 (8-콜레스테릴옥시카보닐)헵타노일 클로라이드와 반응시켜 완전치환 콜레스테릴옥시카본화 그리고 (8-콜레스테릴옥시카보닐)헵타노화 이당류 유도체들을 합성함과 동시에 이들의 열방성 특성들을 검토하였다. 모든 콜레스테릴옥시카본화 유도체들(CH1DSs)은 쌍방성 콜레스테릭 상들을 형성하는 반면 모든 (8-콜레스테릴옥시카보닐)헵타노화 유도체들(CH8DSs)은 좌측방향의 나선구조를 지니며 온도상승에 의해 광학피치들(λm's)이 감소하는 단방성 콜레스테릭 상들을 형성하였다. 모든 CH1DSs들은 CH8DSs들과 달리 콜레스테릭 상의 전 범위에서 반사색깔을 나타내지 않았다. 이러한 사실은 콜레스테릴 그룹에 의한 나선의 비틀림력은 콜레스테릴 그룹과 이당류 사슬을 연결하는 스페이서의 길이에 민감하게 의존함을 시사한다. CH8DSs들에서 관찰되는 액정 상의 열적 안정성과 질서도 그리고 λm의 온도의존성은 콜레스테릴 그룹을 지닌 dimer들과 triplet 그리고 (8-콜레스테릴옥시카보닐)헵타노화 다당류들에 보고된 결과와 전혀 달랐다. 이들의 결과를 반복단위 몰당의 mesogenic 단위들의 수와 주사슬의 유연성의 차이와의 관련하에서 검토하였다.

Keywords: disaccharides; cholesterol; cholesteric phase; optical pitch; helicoidal sense

References
  • 1. Blunk D, Praefcke K, Vill VHandbook of Liquid Crystals, D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess, and V. Vill. Editors, Wiley-VCH, Weinbeim-New York, Vol 3, Chap. VI, p 305 (1998)
  •  
  • 2. Cammidge AN, Bushby RJHandbook of Liquid Crystals, D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess, and V. Vill, Editors, Wiley-VCH, Weinbeim-New York, Vol 2B, Chap. VII, p 693 (1998)
  •  
  • 3. Gray JW, Liq. Cryst., 24, 25 (1998)
  •  
  • 4. Hanemann T, Schumacher E, Haase W, Lichtenthaler FW, Liq. Cryst., 22, 47 (1997)
  •  
  • 5. Van Doren HA, Van Der Heijden AM, De Goede ATJW, Rantwijk FV, Bekkum HV, Liq. Cryst., 27, 63 (2000)
  •  
  • 6. Hein M, Miethchen R, Schwaebisch D, Schick C, Liq. Cryst., 27, 163 (2000)
  •  
  • 7. Zur C, Miller AO, Miethchen R, Liq. Cryst., 24, 695 (1998)
  •  
  • 8. Bault P, Gode P, Goethals G, Goodby JW, Haley JA, Kelly SM, Mehl GH, Ronco G, Villa P, Liq. Cryst., 25, 31 (1998)
  •  
  • 9. John G, Minamikawa H, Masuda M, Shimizu T, Liq. Cryst., 30, 747 (2003)
  •  
  • 10. Jung JH, John G, Yoshida K, Shimizu T, J. Am. Chem. Soc., 124(36), 10674 (2002)
  •  
  • 11. Hein M, Miethchen R, Tetrahedron Lett., 39, 6679 (1998)
  •  
  • 12. Boyd BJ, Krodkiewska I, Drummond CJ, Grieser F, Langmuir, 18(3), 597 (2002)
  •  
  • 13. Fukuda T, Tsujii Y, Miyamoto T, Macromol. Symp., 99, 257 (1995)
  •  
  • 14. Dumoulin F, Lafont D, Boullanger P, Mackenzie G, Mehl GH, Goodby JW, J. Am. Chem. Soc., 124(46), 13737 (2002)
  •  
  • 15. Marcelis ATM, Koudijs A, Sudholter EJR, Liq. Cryst., 18, 851 (1995)
  •  
  • 16. Marcelis ATM, Koudijs A, Sudholter EJR, J. Mater. Chem., 6, 1469 (1996)
  •  
  • 17. Marcelis AT, Koudijs A, Sudholter EJ, Thin Solid Films, 284-285(-), 308 (1996)
  •  
  • 18. Yelamaggad CV, Srikrishna A, Shankar Rao DS, Krishna Prasad S, Liq. Cryst., 26, 1547 (1999)
  •  
  • 19. Cha SW, Jin JI, Laguerre M, Achard MF, Hardouin F, Liq. Cryst., 26, 1325 (1999)
  •  
  • 20. Hardouin F, Achard MF, Laguerre M, Jin JI, Ko DH, Liq. Cryst., 26, 589 (1999)
  •  
  • 21. Lee JW, Park YS, Jin JI, Achard MF, Hardouim F, J. Mater. Chem., 13, 1367 (2003)
  •  
  • 22. Lee KH, Lee JW, Jin JI, Liq. Cryst., 28, 1591 (2001)
  •  
  • 23. Marcelis ATM, Koudijs A, Sudholter EJR, Liq. Cryst., 27, 1515 (2000)
  •  
  • 24. Yelamaggad CV, Hiremath US, Shankar Rao DS, Liq. Cryst., 28, 351 (2001)
  •  
  • 25. Yelamaggad CV, Anitha Nagamani S, Hiremath US, Nair GG, Liq. Cryst., 28, 1009 (2001)
  •  
  • 26. Ajay V, Mallia, Das S, Liq. Cryst., 28, 259 (2001)
  •  
  • 27. Kim KN, Do ED, Kwon YW, Jin JI, Liq. Cryst., 32, 229 (2005)
  •  
  • 28. Marcelis ATM, Koudijs A, Klop EA, Sudholter EJR, Liq. Cryst., 28, 881 (2001)
  •  
  • 29. Cha SW, Jin JI, Achard MF, Hardouin F, Liq. Cryst., 29, 755 (2002)
  •  
  • 30. Yelamaggad CV, Amitha Nagamani S, Fujita T, Iyi N, Liq. Cryst., 29, 1393 (2002)
  •  
  • 31. Yelamaggad CV, Mathews M, Fujita T, Iyi N, Liq. Cryst., 30, 1079 (2003)
  •  
  • 32. Yelamaggad CV, Anita Nagamani S, Hiremath US, Shankar Rao DS, Krishna Prasad S, Mol. Cryst. Liq. Cryst., 397, 207 (2003)
  •  
  • 33. Marcelis ATM, Koudijs A, Sudholter EJR, Mol. Cryst. Liq. Cryst., 411, 193 (2004)
  •  
  • 34. Imrie CT, Luckhurst GRHandbook of Liquid Crystals, D. Demus, J. Goodby, G. W. Gray, M.-W. Spiess, and V. Vill, Editors, Wiley-VCH, Weinheim-New York, Vol 2B, Chap. X. p 801 (1998)
  •  
  • 35. Ma YD, Jeong SY, Choi JH, Industrial Technology Research Paper (Dankook University), 2, 49 (2001)
  •  
  • 36. Abraham S, Mallia VA, Ratheesh KV, Tamaoki N, Das S, J. Am. Chem. Soc., 128(23), 7692 (2006)
  •  
  • 37. Milla VA, Tamaoki N, Chem. Mater., 15, 3237 (2003)
  •  
  • 38. Jin JI, Mol. Cryst. Liq. Cryst., 267(-), 249 (1995)
  •  
  • 39. Tamaoki N, Matsuda H, Takahashi A, Liq. Cryst., 28, 1823 (2001)
  •  
  • 40. Do ED, Kim KN, Kwon YW, Jin JI, Liq. Cryst., 33, 511 (2006)
  •  
  • 41. Le Masurier PJ, Luckhurst GR, Liq. Cryst., 25, 63 (1998)
  •  
  • 42. Blatch AE, Luckhurst GR, Liq. Cryst., 27, 775 (2000)
  •  
  • 43. Yelamaggad CV, Anitha Nagamani S, Hiremath US, Shankar Rao DS, Krishna Rpasad S, Liq. Cryst., 29, 1401 (2002)
  •  
  • 44. Diez S, Dunmur DA, De La Fuente MR, Karahaliou PK, Mehl G, Meyer T, Jubindo MAP, Photinos DJ, Liq. Cryst., 30, 1021 (2003)
  •  
  • 45. Yelamaggad CV, Mathews M, Hiremath US, Nair GG, Shankar Rao DS, Krishna Prasad S, Liq. Cryst., 30, 899 (2003)
  •  
  • 46. Pfeutter T, Hanft D, Strohriegl P, Liq. Cryst., 29, 1555 (2002)
  •  
  • 47. Del Campo A, Meyer A, Perez E, Bello A, Liq. Cryst., 31, 109 (2004)
  •  
  • 48. So BK, Jang MC, Park JH, Lee KY, Song HH, Lee SM, Opt. Mater., 21, 685 (2002)
  •  
  • 49. Henderson PA, Imrie CT, Macromolecules, 38(8), 3307 (2005)
  •  
  • 50. Takaragi A, Sugiura M, Minoda M, Miyamoto T, Watanabe J, Macromol. Chem. Phys., 198, 2583 (1997)
  •  
  • 51. Laurent N, Lafont D, Dumoulin F, Boullanger P, Mackenzie G, Kouwer PHJ, Goodby JW, J. Am. Chem. Soc., 125(50), 15499 (2003)
  •  
  • 52. Kim JH, Ma YD, J. Korean Ind. Eng. Chem., 15(1), 113 (2004)
  •  
  • 53. Kim JH, Jeong SY, Ma YD, Polym.(Korea), 28(1), 92 (2004)
  •  
  • 54. Kim JH, Jeong SY, Ma YD, Polym.(Korea), 28(1), 41 (2004)
  •  
  • 55. Jeong SY, Ma YD, Polym.(Korea), 30(4), 338 (2006)
  •  
  • 56. Jeong SY, Jeong JH, Ma YD, Tsujii Y, Polym.(Korea), 25(2), 279 (2001)
  •  
  • 57. Jeong SY, Ma YD, Polym.(Korea), 30(1), 35 (2006)
  •  
  • 58. Shoji K, Nakajima Y, Ueda E, Takeda M, Polym. J., 17, 1029 (1985)
  •  
  • 59. Oishi T, Otsubo Y, Fujimoto M, Polym. J., 24, 527 (1992)
  •  
  • 60. Yao N, Jamieson AM, Polymer, 41(8), 2925 (2000)
  •  
  • 61. Mihara T, Uedaira T, Koide N, Liq. Cryst., 29, 855 (2002)
  •  
  • 62. Sugiura M, Minoda M, Watanabe J, Fukuda T, Miyamoto T, Bull. Chem. Soc. Jpn., 65, 1939 (1992)
  •  
  • 63. Jeong SY, Ma YDto be pulished
  •  
  • 64. Kim KH, Jeong SY, Ma YD, Polym.(Korea), 25(4), 545 (2001)
  •  
  • 65. Ogawa H, Stibal-Fischer E, Finkelmann H, Macromol. Chem. Phys., 205, 593 (2004)
  •  
  • 66. Liu LM, Zhang BY, Cheng CS, Zheng YY, J. Appl. Polym. Sci., 91(2), 773 (2004)
  •  
  • 67. Hu JS, Zhang BY, Jia YG, Yang Y, Polym. J., 35, 160 (2003)
  •  
  • 68. Zhang BY, Hu JS, Jia YG, Du BG, Macromol. Chem. Phys., 204, 2123 (2003)
  •  
  • 69. Hu JS, Zhang BY, Jia YG, Chem S, Macromolecules, 36 (2003)
  •  
  • 70. Zang BL, Hu JS, Meng FB, Zhang BY, J. Appl. Polym. Sci., 93(6), 2511 (2004)
  •  
  • 71. Oh CIM. Sc, Dissertation, Dankook University (1996)
  •  
  • 72. Jeong HM. Sc. Dissertation, Dankook University (1997)
  •  
  • 73. Jeong SY, Ma YDunpublished results
  •  
  • 74. Branolenburger F, Matthes B, Seifert K, Strohriegl P, Liq. Cryst., 28, 1035 (2001)
  •  
  • 75. Piao XL, Kim JS, Yun YK, Jin JI, Hong SK, Macromolecules, 30(8), 2294 (1997)
  •  
  • 76. Percec V, Asandei AD, Hill DH, Crawford D, Macromolecules, 32(8), 2597 (1999)
  •  
  • 77. Lee JW, Jin JI, Jo BW, Kim JS, Zin WC, Kang YS, Acta Polym., 50, 399 (1999)
  •  
  • 78. Lam JWY, Kong XX, Dong YP, Cheuk KKL, Xu KT, Tang BZ, Macromolecules, 33(14), 5027 (2000)
  •  
  • 79. Takada A, Fujii K, Watanabe J, Fukuda T, Miyamoto T, Macromolecules, 27(6), 1651 (1994)
  •  
  • 80. Qu X, Wirsen A, Albertsson AC, Polymer, 41(13), 4841 (2000)
  •  
  • 81. Rath SK, Singh RP, J. Appl. Polym. Sci., 70(9), 1795 (1998)
  •  
  • 82. Xiao CB, Gao SJ, Zhang LN, J. Appl. Polym. Sci., 77(3), 617 (2000)
  •  
  • 83. Athawale VD, Rathi SC, Eur. Phys. J., 33, 1067 (1997)
  •  
  • 84. Xiao CB, Lu YS, Liu HJ, Zhang L, J. Appl. Polym. Sci., 80(1), 26 (2001)
  •  
  • 85. Hatakeyama H, Izuta Y, Macromol. Symp., 130, 127 (1998)
  •  
  • 86. Guo JX, Gray DGCellulosic Polymers, Blends and Composites, R. D. Gilbert, Editor, Hanser Verlag, Munich, Chap. 3, p 25 (1994)
  •  
  • 87. Kondo T, Miyamoto T, Polymer, 39(5), 1123 (1998)
  •  
  • 88. Ma YD, Jeong SY, Industrial Technology Research Paper (Dankook University), 5, 21 (2004)
  •  
  • 89. Ma YD, Jeong SY, Industrial Technology Research Paper (Dankook University), 6, 21 (2005)
  •  
  • 90. Ma YD, Jeong SY, Industrial Technology Research Paper (Dankook University), 6, 1 (2005)
  •  
  • 91. de Vires H, Acta Crystallogr., 4, 219 (1951)
  •  
  • 92. Jeong SY, Choi JH, Ma YD, Polym.(Korea), 26(4), 523 (2002)
  •  
  • Polymer(Korea) 폴리머
  • Frequency : Bimonthly(odd)
    ISSN 0379-153X(Print)
    ISSN 2234-8077(Online)
    Abbr. Polym. Korea
  • 2022 Impact Factor : 0.4
  • Indexed in SCIE

This Article

  • 2007; 31(1): 58-67

    Published online Jan 25, 2007

  • Received on Oct 11, 2006
  • Accepted on Dec 5, 2006